Flights Chicago → Boston — September 19, 2026

One way · Economy · 1 adult · price per person

The cheapest itinerary observed for Saturday, September 19, 2026 on the Chicago–Boston route: 1 stop itinerary (2 flights) via Orlando International (MCO), from Chicago O'Hare (ORD) to Boston Logan (BOS), first flight Frontier Airlines F93044, departs 3:50 PM, arrives 10:58 AM the next day, total travel time 18h 8m including layovers, flight time 6h 2m (layovers excluded), $140 per person. Fare as listed by Aviasales: carry-on bag not included (personal item only), checked bag not included, changes not allowed, non-refundable. Price found in an Aviasales search on September 9, 2026 and read by AirSource on September 10, 2026, 20:47 UTC: it is not guaranteed and is confirmed on Aviasales at booking time. The cheapest direct flight observed: Southwest Airlines WN3329, from Chicago Midway (MDW) to Boston Logan (BOS), departs 3:10 PM, arrives 6:35 PM, direct, 2h 25m, $167 per person. Fare as listed by Aviasales: carry-on bag not included (personal item only), checked bag not included, changes not allowed, non-refundable.